Today's guest is the former MTV video jockey and current Fox News personality Kennedy, who emerged in the 1990s as a leading voice of Gen X when it came to politics and culture. Reason's Nick Gillespie talks with her about how a generation raised on neglect, nuclear nightmares, and Nirvana forged an ethos of irreverence and independence that still matters today. Kennedy explains her evolution from a teen Republican who swooned over Dan Quayle to a principled libertarian, why the culture of alternative music and media once felt so alive and vital, and what it means when former pop culture rebels like Jimmy Kimmel and Howard Stern become defenders of the status quo. She also talks about free-range parenting and why more of us need to stop caring about what others think and let everyone live radically on their own terms.

0:00—Introduction

2:30—What was MTV like when Clinton was elected president?

730—How did Kennedy become a 'self-declared libertarian'?

12:20—What is the most appealing about libertarianism?

15:01—How did being 'alternative' become mainstream?

22:07—What was it like being a public virgin?

25:42—What is the Gen X ethos?

31:22—Why you can make fun of everything

36:58—How Jimmy Kimmel and Adam Carolla went down vastly different paths

41:07—What is it like to work at Fox News?

47:25—Are conspiracy theories fun?

Upcoming events:

Today's sponsor:

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Transcript

This is an AI-generated, AI-edited transcript. Check all quotes against the audio for accuracy.

Nick Gillespie: This is The Reason Interview With Nick Gillespie.

All right, so we know the names, right? The single-named beings that stride our planet like latter-day gods—Madonna, Prince, Sting, Björk, Liberace, and, of course, Kennedy, my guest tonight. Kennedy, thanks for talking.

Kennedy: Thank you, and thank you, Nick Gillespie.

I'm not sure which name I want to get—should I get rid of Nick or Gillespie or come up with something new? Evita's up for grabs.

Evita Portmanteau, I think. Evita.

Evita, right? Let's talk about the early days of Kennedy as a public figure. You started working at MTV around 1992.

Correct. It was September of 1992, right before Bill Clinton was elected.

Yeah. I want to spend a lot of time talking about Gen X. Even though I am a part of the baby boom, I've become possessed with the idea that Gen X is the best generation, and its characteristics are what we need in America today.

But before we get to that, because you mentioned Bill Clinton and that was the big generational shift—he was the first baby boom president—can you paint a scene? What was it like at MTV when Bill Clinton won the presidency?

It was so hopeful. People were so optimistic in New York, and, of course, MTV at the time was populated by East Coast elites, big-city liberals. A lot of people had gone to places like Yale and Dartmouth, and a lot of Emerson College graduates were at MTV, and they were ready—

So, a lot of miming in the hallway.

Yeah, so much mummenschanz.

And they were ready for their president. The MTV News department, which was fairly new and gaining influence at that time, they were putting a lot of money and resources into MTV News and wanted to cover the political campaign in a new way for this generation—who were just interfacing with politics and news for the first time.

When Bill Clinton was elected, they didn't really pay attention to the data. They just looked at everything and looked at all the coverage, the publicity that the Choose or Lose campaign got—and they were like, "Well, MTV elected Bill Clinton. And you are so welcome."

They didn't talk about Ross Perot. They didn't talk about the 12 years of the Reagan-Bush era. It was just like, "no, MTV was here and ordained Bill Clinton as president." It was a massive shift.

It's hard to recover that, and I think we're going through something similar now—which will probably fully come online in a couple years—where it's the first millennial president or something.

But you were the resident Republican at MTV. What were you thinking? And why were you a Republican, and what did that mean to you?

I was a Republican because I grew up in Oregon where everyone was liberal, and the people who were really into politics didn't seem particularly happy.

There was a kid at my high school named Creighton Webb who was the president of the Teen Republicans. He invited me to go to a couple of chapter meetings, and then he invited me to meet Dan Quayle in Portland when I was a senior in high school.

And you famously kind of splooged over Dan Quayle, didn't you? He was a handsome, robust young man.

I'm not going to say that it was externally ejaculatory, but I will say that I felt like there was such a connection between us. I think when you feel a connection like that—and any stalker can co-sign this—it can't be one-sided.

When you feel something that deeply and that intensely with another human being, obviously they feel the same thing for you. There's that famous Mookie Wilson fake quote: "Whenever I'm going through a slump, I just think about dinosaurs. And then I think, if I'm thinking about dinosaurs, then somewhere the dinosaurs are thinking about me. And if the dinosaurs believe in me, then I can believe in me. And all of a sudden I feel better."

It's a totally fake quote, but it's one of my favorite things in the world. That's how I felt about Dan Quayle.

So, what was—beyond being contrarian—the appeal of being a Republican?

I mean, it really was, at that point in my kind of immature, developing brain, it just made people so mad.

I had this one English teacher—

This is a great part of Gen X.

Yeah, I mean, I had this one English teacher who was such a blowhard and he was such a liberal. He talked about going to Tibet and throwing himself naked on the side of a mountain.

And he failed me, and I hated him with a blinding passion. The thing he really hated about me was that I started cavorting with the Teen Republicans. They were really fun. They were rabble-rousers.

I compare it to young men in high school and college today who wear MAGA hats. They don't necessarily believe in the Trump doctrine—whatever that means for them—but they just know their constipated, liberal social studies teacher in high school, nothing makes them seethe like this. And there's something really satisfying about that. I think there has to be something utilitarian about making people you don't respect that angry.

I'll put that in terms of evolutionary biology where the people who did that did not get eaten by the lions or something—I don't know.

But you then evolved—and you evolved upward—to a libertarian position, partly because of the people you met at MTV. Can you talk a little bit about what took you from being a kind of oppositional or contrarian Republican to a self-declared libertarian?

Yeah, there was a lot of stuff that I liked about the Republican Party in 1992 and 1993 because it became the opposition party. But what I didn't like about it was I had a lot of gay friends—especially being in New York, being young, being in music—and I didn't like the way that, you know, because Jesse Helms was still alive, and one of his famous quotes was, "You become what you condone." And I'm like…

Oh, wow.

I don't think I'm going to become a gay man anytime soon.

I mean you still got—

But right now, like, I totally could. I could be like, "Tomorrow, I'm a gay man." They'd be like, "Great. We're going to throw you a parade. Congratulations."

But the social conservatism was really off-putting. I liked the idea of aspirational success. I was having dinner with Kurt Loder one night, and he was like, "You're not a Republican." He was getting really frustrated. He was very angry about the Clinton White House and was disgusted by what he saw as encroaching big government.

And I was like, "I hate that stuff too." But he's like, "You're a libertarian." I didn't know what that meant, but I was very intrigued by the idea because I was also very good friends with Dweezil Zappa, and we would sit and talk with his father, Frank, who at the time was being treated for metastatic prostate cancer.

He would lose his battle with that the year after I met him. But listening to Frank—because we wouldn't talk; I didn't have a lot to add to the discussion—but listening to Frank…

I get the impression too that Frank Zappa didn't really need people to fill the pauses.

He didn't. He was a very interesting person. Loved coffee. He talked about libertarianism, and he was really interesting in the way Kurt Loder was really interesting. They both were energized and super-powered by music.

Obviously, Frank Zappa was creating music in a way that no one ever had, and musicians that I love respected him so much. And Kurt Loder analyzed and understood music in the way a critically thinking journalist would. He didn't have to make music to really want to exist inside of it, take it apart, and explain it to people.

So if both of those people—who were infinitely smarter and more experienced than me—had a name for the same kind of conclusion, and one of them was saying, "You're a libertarian" as well, then I wanted to investigate that.

And you have mentioned that Kurt gave you an Ayn Rand book.

And I still have it. I rescued it—

And you became a libertarian regardless.

Yeah, exactly. So I have a home in Pacific Palisades that is uninhabitable. It is filled with lead and asbestos, and the insurance company is trying to deny our claim. Everything around us burned—three houses in either direction.

Everything around us burned. The back door blew open, and that means that every microwave, every piece of siding, every Tesla, everything in the neighborhood burned. The incineration and the aftermath filled our house, as it did with the people who were fortunate enough to keep their homes.

Pretty much everything in the house has to be thrown away. And there were two books that I—well, there are three. A really, really old edition of Les Misérables in French, and Emmanuel was like, "Oh mon Dieu, c'est fantastique." One was, of course, I found the copy that Kurt gave me of Objectivist Epistemology.

And the other was a book called You Are the Message. I had it autographed by the author in 1993 when he and I were co-panelists on one of the earliest episodes of Politically Incorrect, which at the time was on Comedy Central.

The inscription on the book is, "Dear Kennedy, I think you're fantastic. Do you fool around?"

Yeah and wait for the punch line, that book was written by Roger Ailes.

And no, I didn't fool around. There was no fooling around. And as Mary Katharine Ham pointed out years later, he didn't really have a thing for quirky libertarian brunettes.

Yeah, that's not his type. What was it about libertarianism that appealed to you then?

Freedom.

Like the freedom to be successful, the freedom to make academic inquiry without being married to groupthink, and the freedom to allow people to do whatever they wanted because I saw so much of that going on around me in music.

As long as it didn't affect me, you know, there was a relationship between debauchery and creativity that I always found so fascinating. That intersection was so rich because it could be chaotic and destructive and deadly, or it could be mind-blowing and soul-shaking and beautiful.

A lot of the social conservatives they did condemn that. They condemned music, they condemned lyrics, and they condemned partying of any kind. Even though I was really straight-edged at the time, I loved being around people who rode the razor's edge.

Did the people in the music industry or in entertainment industry—they wanted creativity and the freedom to create, but their politics tended to be the most suffocating form of, "Well, I should be allowed to do what I want, but you… you have to turn your thermostat down, you have to drive this kind of car, work this kind of way"? How does that kind of cognitive dissonance maintain itself?

I think it sort of dies for a little bit and hibernates, and then it comes back. It comes back as Occupy Wall Street, and now it is regenerated and reanimated as "The Squad."

You see this progressivism which obviously wants to increase the size and power of the state, but at the same time there's an edict. There are these arbitrary rules that you must live by. And if you're not, you're the other. You are a bad person, and you must be conquered and crushed. You can't go on private jets. You can't build skyscrapers. You can't use gas stoves, but "I'm going to go cook a video on Instagram Live and it's gonna be on my gas stove because I'm so amazing. Let's go celebrate the global intifada."

You know, the show that you…

That's Chuck Schumer, by the way.

I'm glad somebody knew who that was.

The show that you hosted on MTV—I mean, you were on a bunch of things—but it was called Alternative Nation. One of the things that was kind of great about the '90s was that alternative music became mainstream. It was the mainstream. There was no mainstream anymore.

There was a period of time where things that were labeled "alternative" were the bestselling type of music. And throughout the culture, there was a real celebration of people hiving off and experimenting and doing their own thing and moving away from the old gods and creating new gods, and then smashing those idols and moving on.

What do you think went into that? And is that something we should be striving to recapture?

I don't know if you can recapture it because so much of what people do now is just to be seen. So much of what was great about that scene was like dudes who now would be called "incels," locking themselves in garages and basements and just experimenting with chords, putting their sad poems and their quirky poems to music.

Then getting together with a couple of friends—like, "screw it, let's go play an open mic night and see if we can get anything going at this bar." Slowly and organically building a following. Then you tour. You get a crappy van and you start driving around the country, sleeping on friends' floors. The second time around, your van's a little bit bigger.

It turned out that there was such an appetite for that sort of isolated and beautiful creation that it just—in spite of itself, in spite of being repulsed by fame—absolutely exploded and became its own monster that could not be killed or tamed.

This puts me in mind of the story that you've told me—that you were prank phone called by Kurt Cobain of Nirvana. What was the nature of the prank phone call?

So Pat Smear and I were friends, and Pat was—

He was the touring guitarist for Nirvana. He's now in the Foo Fighters and was in the great L.A. punk band The Germs, which burned too brightly—let's put it that way.

Yeah. So Pat and I became friends, and Kurt was like, "You have her number?" And Pat's like, "Yes." And he's like, "Let's prank call her." And Pat's like, "No, she's my friend, I can't." And Kurt's like, "I'll fire you from the band." And he was like, "Okay, here it is."

At the time, I got prank called by so many people that I was used to getting prank calls that someone would call and be like, "Is your refrigerator running?" And I'd say, "Yeah, and your mom's balls are in it." I would prank the people right back. So I did that with him, and he didn't know what to do.

And he was so sensitive.

He's very sensitive. So he hung up. And we know how everything ended and I blame myself.

Toward the end of…

Too soon.

I think Kurt Cobain would be the first person to say it's never too soon, right?

Courtney Love gave out my phone number one night on stage. And for that, she's a filthy crack whore—because I had to change my number. But at the time, it took so long to get your number changed that I had to spend a week taking calls like, "Courtney gave out your number!"

So my outgoing message was like…"Hello, you have reached Dr. Rothbaum, plastic surgery for the energetically ugly. Please leave your message at the tone."

It was a simpler time, wasn't it?

Yes.

At the end of the '90s, you wrote a book called Hey Ladies! which was advice for young women at the time. What was the main message of that, and do you think it still holds up?

The main message was: try not to get boob jobs or give too many blow jobs, and earn as much money as you can and just get rad. And then if that doesn't work out, go become a nun. That was the message.

I mean, it really is like—it's all about, like, don't disfigure yourself. Like, you're really beautiful no matter what. And you can still get herpes from mouth love.

I think we've solved that problem. Nobody talks about herpes anymore, right?

So, I have teenage daughters, and that was how I scared them. Because I really think—my mom's Romanian, and guilt and superstition are such phenomenal tools. Parents are so worried about being friends with their kids now that they don't use them effectively.

But I told my daughters, like, "OK, if a boy is going to put his penis in your mouth, he has put it in another girl's bottom. And there are butthole warts that you can actually get in your throat. So just be careful. Just think about that."

Now I understand why Gen Z doesn't have sex.

Exactly!

You were a kind of professional virgin for a while when you emerged—a Republican and a virgin.

Wasn't for a lack of trying, but yeah, that's true.

What was being a public virgin about?

It was about being obnoxious and not being able to seal the deal. Yeah. So it wasn't like, "I'm just going to wait forever." It's like, "No, seriously, anyone—literally anyone. You, J Mascis? No? Ok. Very good."

So I guess I was the incel.

But no, it wasn't….So my name on KROQ—which was the radio station where I started, which became a feeder station for MTV, because Adam Carolla and Jimmy Kimmel started there, Carson Daly started there, Louis Largent—God rest his soul—who was the music director when I was there, he went on to host 120 Minutes at MTV. Our program director, Andy Schuon, who got hired at MTV in the spring of 1992, hired us all and brought us over one by one.

So when I was on KROQ at the time, like, I had not had marital man-woman relations. And we were trying to come up with a radio name because, you know, you have to have a quirky radio name. Our morning show was Kevin and Bean. It's like, "It's Rocktober Two-For-Tuesday, folks! Be funny or be quiet. Be better than the music."

So you had to have a kitschy radio name. They were like, "How about the Virgin Kennedy?" And I was like, "Well, it fits."

OK, there you go. When did you drop that?

"The Virgin Kennedy"? When I got to MTV. Andy thought it was really funny. Everyone—like the Emerson suits at MTV—were like, "No, that's stupid. That sounds like a radio name. This is not radio."

"No, this is MTV. Go get some conditioner in your hair."

What were your favorite bands in the MTV period? Who were the ones that you would die for?

Die for? Rocket from the Crypt, absolutely. The entire '90s San Diego punk rock scene, I think, is one of the most perfect eras in music.

Rocket from the Crypt from…

San Diego.

San Diego, not Cleveland.

No, Rocket from the Crypt was in San Diego, California, along with Drive Like Jehu, Olive Lawn, Pitchfork. They were amazing. I have a Rocket from the Crypt tattoo.

Oh, I'm sorry, I was thinking of Rocket From the Tombs. Like Cleveland….Excuse me.

Yeah, no.

I'm having a senior moment here.

That's OK. Maybe that's where they took their name. But I have a Rocket from the Crypt tattoo. So in the '90s, if you had this tattoo, you could get into all their shows for free. And they were like, "We want MTV to play our music, so we would let you in for free anyway, hoping that you put in a good word with your bosses." But I didn't know that, so…

Yeah, yeah. So—

And I loved Mudhoney as well.

There you go.

And Rancid.

Yeah. Are you done?

And I guess we can think of things all night. I wasn't wild about Pearl Jam.

No? Why not? What didn't you like about it?

I felt that they were so pissy—like, "We don't want MTV. We don't want to do anything on MTV. We're so cool because we're in Seattle." And then I sold my house to Stone Gossard. Now I really like Pearl Jam.

I like the way that in the name of not selling out, they always made it more complicated for their fans to buy tickets.

Yeah, exactly.

And things like that, because they wouldn't use Ticketron. "Fuck Ticketron," or Ticketmaster now, right? Instead, go out and stand in line in the middle of the night somewhere.

Yeah, now they play arenas in South America and make $20 million a show.

So talk a bit about the Gen X ethos. You know, part of it is being contrarian. Part of it is being against whoever is in charge. Part of it is being DIY. How did that play out in your early career and in your life?

I've always thought that Gen X was really amazing and fascinating. I remember having this discussion with one of the executives at MTV—he was only a few years older than me, maybe six or seven years older—but we had disagreements about why our generation was the way it was.

I was like, "It's because we lived under the threat of nuclear holocaust." We always thought, you know, like Sting sang, "I hope the Russians love their children too, because they're going to kill us any day. Get under your desk." We always just assumed we were going to die in a nuclear holocaust.

So either you're nihilistic and you're like, "Well, then I have nothing to live for," or, "Dude, we're going to die at any second, so let's go light some shit on fire."

Those were the people I grew up with. "Let's sneak out and TP someone's house and then go see a rock show." Part of it was the fear of imminent destruction. And the other part, which I always thought was so curious, was just total neglect.

Your mom would leave you with a loaf of Wonder Bread and a brick of Velveeta and call it good. We were all latchkey kids. A lot of kids—especially in the late '70s and '80s—their parents who got divorced. They abandoned the '50s as fast as they could.

They ran for the exits.

So they had these traditional upbringings with aprons and apple pie. And the second they could be like, "OK, you guys just come home at night, we kind of didn't give a shit what happened to you at all."

That's how we were raised. We were mongrels. We were little heathens trying to piece stuff together. I remember so much of my childhood was coming up with elaborate pranks that really disturbed people, throwing things at cars, and lighting things on fire.

Every Fourth of July, my dad would give us a bag of fireworks and each of us a lighter and would say, "Go have fun." Now I look back and part of me thinks it's neglect—and part of me thinks our parents were actually trying to kill us. "Go all get on your bicycles and ride around and try and find a rabid dog." You don't have cellphones. You have no way of communicating. And if one of the neighbors hits you—one of their parents? "I'm good with it."

Oh, they're probably right. Did you raise your kids that way, or are you raising your kids some way?

Kind of. I definitely love the idea of free-range parenting, but it still scares the crap out of me being in New York. As parents with kids in the city, they see things constantly. They're always like, "Yeah, I saw a guy pooping on the subway." And it's like, "Yeah, I saw that like three times last week. That's such a boring story. Please come up with something new."

And then the other night, my daughter and her friend were in a yellow cab, and the cab driver locked them in the cab. They had the wherewithal to call my handsome teenage boyfriend and texted him, "Pretend you're a cop."

He answered the phone, and my older daughter was like, "You're the cop, right?" And he, in his authoritative voice, convinced the cab driver to unlock the cab. He then got out and chased them. Luckily, a deli owner came out, intervened, and offered to pay the cab driver money. Then they had to call the cops.

Was the cab driver completely unmotivated in this, or what was going on with your daughters?

I mean, you know, they were probably asking for it.

Yeah. I'm sure. That's very strange.

I'm just kidding. I'm kidding.

But these are the things—you want to be loosey-goosey, Lenore Skenazy-style and be like, "Yeah, just let my kids ride the subway from the time they're four months old." And it's like, "there are people around, they'll probably be fine."

They should be driving cabs by the time they're 13, right? Forget about being on the subway.

Driver's licenses are a societal convention….We don't really need any licensing, but yes. In a way, yes.

The most freeing thing as a parent was when I could finally start swearing in front of my children. Because then I felt like I could be myself and they finally could know me.

I was telling Joanna and Emmanuel earlier—we were talking about a group of parents discussing progressivism in New York schools—and I said, "Well, my daughter goes to a public school."

And another parent was like, "It doesn't matter where they go. It could be a private school, it could be an upscale private school—they're all progressive. Their minds are all warped."

I always say that my children were saved when they started watching South Park. They realized: It's fun to swear. It's fun to make fun of everything. And nothing is sacred.

How do you turn that "nothing is sacred" and "having fun"—and this is a great Gen X dimension, right? Just making fun of everything all the time….Does that become corrosive, how do you turn that into where you stand for, as opposed to just constantly knocking things?

You can make fun of everything. And that's what makes it safe. It's sort of the antidote to cynicism.

Cynicism is awful. Cynicism—and I should say bitterness—those are the corrosive elements. That comes from stasis, where you're constantly angry about everything and you're utterly joyless.

You look at the world and everything is bad and everyone is horrible, and you should feel very guilty for everything.

That's the opposite of, "Let's have some fun. Let's make fun of everything." Of course, you have to point that lens at yourself. Self-deprecation is very powerful and a bonding experience when everyone can just roast each other.

Like, what would you rather do—watch the roast of David Hasselhoff or go to a Bernie Sanders rally?

I'm going to go with David Hasselhoff.

Yeah, me too.

Even if he's eating burgers off the floor.

It's kind of sexy.

Yeah. Wow.

It's keto.

That's right.

Probably bison.

If we come to the current moment—where has that ability to make fun of everything gone? Because it seems like on the left, certain things are sacred and can never be talked about. And now, particularly with the re-election of Donald Trump, the same thing—nobody is willing within the Trump wing to make fun of Trump.

Yes, and make fun of everything. You know, the thing that bummed me out was Sarah Silverman and Amy Schumer apologizing for their acts.

I was like, how dare you? To me, that was almost like heresy.

The jokes you created that were so outlandish—and that's how you established your name—now you're distancing yourself from the humor that made you what you are. That was your identity: the ability to pointedly say anything and make fun of anyone.

They're like, "Oh, well, we shouldn't say that."

One of my heroes, Howard Stern—what he has become, being consumed by political correctness—it's so sad to see. Him apologizing for bits he did in the '80s and '90s.

Sure, they're off-color and gross. But at least give yourself the dignity to acknowledge that's where we were at that time. That's how people made each other laugh.

With somebody like Howard Stern—who really transformed radio and a lot of other talk media—he had a couple of great interview shows on the E! Channel. He did a New Year's Eve special with, among other things, Sherman Hemsley from The Jeffersons, which is now, nobody talks about it. It was remarkable. It was pay-per-view. I have a VHS of it somewhere slowly turning into vinegar—and it's beautiful.

What happens with people like that, where they go from being the person who gives no fucks to the person interviewing Joe Biden and coaching him through his answers?

Yeah. When did he become Eva Braun?

No, but the point is, the old Howard Stern would point out Joe Biden's dementia and probably have Sal and Fred and everyone else writing funny bits about how Joe Biden was pooping his pants in the Rose Garden. But now that he is this cultural codependent, it says a lot. It says a lot about the people they surround themselves with—who make them feel like unless they abide by this progressive orthodoxy, they're bad people and they're to blame for everything—and they sort of buy into it.

Jimmy Kimmel's the same way. Jimmy Kimmel and Adam Carolla are still best friends, but they have completely diverged from one another.

So this is like the old movie Angels With Dirty Faces, where Jimmy Cagney gets caught by the cops and goes to prison and becomes a gangster, and Pat O'Brien becomes a priest. Talk a little bit about that. That's kind of interesting.

Kennedy: Do you mean Pat O'Brien from Access Hollywood?

No, he was no priest, let me tell you. I mean Pat O'Brien the old moon-faced actor.

Remember when Pat O'Brien, when that tape came out?

Absolutely.

He drove by me and I started screaming lines from that tape. And he accelerated. He must have been doing 85 in a 20.

And he was probably drunk to the gills too.

Yeah. And, you know, probably had a little bit of a Brentwood speedball before he showed up.

What happened that Adam Carolla went one direction—and did not just say stayed true to himsleld—but he created this vast alternative podcast media empire. Jimmy Kimmel hits the jackpot in the old legacy media thing. Can you just kind of talk a little about that?

Yeah. So do you remember the Nicole Kidman movie To Die For?

Yeah, absolutely.

So Nicole Kidman—her whole thing, she was a local newscaster and she just wanted to go network. She wanted to go network so badly, she literally would have killed her own mom.

And she didn't care who got in her way.

Nope. She was just going to do it. And that was Jimmy Kimmel. He went the Nicole Kidman route and was like, "I'm going to appeal to the suits at Disney and ABC. I'm going to sanitize my comedy and my image and get a hair system."

And Adam was just like—

I mean, they were on The Man Show.

The Man Show. So Jimmy Kimmel made his name watching girls jump on trampolines so you could see their boobs bounce. That's how he made his name. It's like, how could you abandon that? Where are your principles, sir?

He's going to wake up one day and wonder where it all went. What about Adam Carolla?

I think Adam is a genius. Adam saw past radio. Everyone at the time was like, "Oh, we've got to get Howard's stations. If we get Howard's stations, we're going to be worth $100 million in a couple of years." But Howard leaving Sirius just accelerated the push into new media.

Can I tell you a really funny story very quickly?

I don't think we have time for it, but OK.

So Andy—who was my program director at MTV, who hired us all to go to MTV—a few years after he left MTV, he was general manager at Warner Bros. Music. Then he was in charge of something called PressPlay, which I think was a music device at Sony.

He always had his eye on new media. Very smart guy—same way as Carolla. So Steve Jobs was like, "I want to meet with you. I want to talk to you. I want to see if maybe you'd be a good fit for us here at Apple."

So Andy went and met with him. He spent three hours in the glass office just waiting. He could see Steve Jobs going up and down the hallway, talking on the phone. It was like a form of psychological torture. He thought, "Well, this is odd."

Finally, he goes in and meets with Steve Jobs. Jobs has his résumé—God rest his soul, visionary, pioneer—and he's looking at it and going, "Shit. This is shit. That's shit. Shit, shit, shit." He's like, "Jesus, man. Everything you've done since MTV is shit."

Then he's like, "Do you have anything new for me?"

Andy was like, "Yeah, actually. I've always had this idea that listening to someone on talk radio shouldn't be something that you only listen to at a certain hour of the day when it's broadcast. What if there's a talk radio person, and you really like what they're saying, and you listen to their monologue like a song—and you could carry it around with you on an iPod?"

And Steve Jobs was like, "That's the stupidest idea I've ever heard."

A couple months later, Apple launched podcasts.

Yeah. Wow. Let's talk about at Fox News now.

And Adam was the same way. Adam said, "Don't chase Howard's ghost. Create your own thing." He knew he wanted to have conversations in a new way. Adam Curry was the same way.

They were convinced that they could talk to people the way they wanted to in a longer format—and not be chained to the radio clock, which is, "OK, we're out at :58. It's a hard out." Traffic and weather together on the ones.

You've got to speed up at the end and cut people off and all that. You've been at Fox News now for…when did you join Fox?

2012.

Right. You did a number of shows, including The Independents with Reason's own Matt Welch. And then your own show, Kennedy. Now you're on The Five, and you're on a variety of other shows. And you do Kennedy Saves the World. Is that through Fox?

Yes. That's a Fox News podcast.

What does it feel like? When Fox created its network in, what, 1996, I think—something like that—that was kind of cutting-edge new media. Cable news.

I mean, CNN had been around and MSNBC was floating around. But now cable is kind of the old media, right? How does it feel to have started at MTV, which was kind of an upstart, and now you're at the Cadillac brand of cable news?

And I mean Cadillac not only in the sense that it's the best—but it's best in the way someone in the 1950s thought of Cadillacs. Nobody talks about wanting the Cadillac of anything anymore.

How does that feel? Do you feel like you're in some kind of loop or something? What's it like to be at legacy media now?

It's fascinating. Fox is putting a lot of emphasis on Fox Nation, which is their digital space. It's a subscriber space. And Fox Digital, and the podcasts—which, as you know, podcasts are video now. They're not just auditory experiences.

I'm waiting for them to become olfactory. Then it's a triple threat.

Listen and sniff with Nick Gillespie.

Just go left.

The axiomatic mononym known as Gillespie.

That's right. Do you have any pressure at Fox to not be too anti-Trump?

No, they're really good about that. The pressure doesn't come from within. The anger comes from out there.

When I say something anti-Trump—or say something that's the actual truth or data-driven—then people are like, "You're anti-MAGA, and you should be canceled. I'm never watching when you're on ever again."

It's like, yeah, you will, Grandpa. Just take some Relaxium. You'll be there for me. And then I'll say something nice about Tiffany Trump, and they'll be like, "You're a patriot."

How do you prepare for today's politics? You talk about politics all the time, and today's politicians are insane. The only thing we know is they're not as bad as tomorrow's will be. What kind of drugs are you taking, I guess is what I'm asking?

Not as many as I should. You know, it's the damn fentanyl. It used to be you could go get a bump and a martini at lunchtime, but boy, they've really thrown a wet blanket on that yard party.

I try and read—I obviously read the Daily Mail.

Yeah, where you're a columnist.

Yes.

What's your latest column?

About Brigitte Macron being a pedophile.

But she is a woman.

Totally. She's like so womanly.

OK.

And she was like—yeah.

You're not just throwing that out there. What do you mean by saying she's a pedophile?

Well, she groomed a 15-year-old boy.

Well, if that's going to be pedophilia…

Yeah, but it's funny because all these Gen Z French kids are reading this stuff like, "What? She was 39 and he was 15?" And then his parents were like, "This is super gross. We're taking you out of school, and you're going to finish high school in Paris." And she was like, "Well, I think I could find myself free on the weekends to do your laundry."

Le weekend.

She would follow him on le weekends, where they would play hide the sausage.

What's the import of that in contemporary America?

I think she's their Mary Kay Letourneau.

Do people remember Mary Kay Letourneau? No?

She was a middle school teacher who raped her 11-year-old student and got pregnant with two of his daughters in prison—one of them, yeah.

Did you miss that, America?

I was living in Seattle at the time, and one year for Halloween I went as Mary Kay Letourneau. I made my then-boyfriend dress up as Vili Fualaau in overalls with a lunch pail and little freckles on his nose.

But they're no longer together, right?

She is no longer living.

Well, that would be a problem. Yeah. So I guess, as a final question before we go to audience Q&A: What's next for Kennedy? What do you think is the big story or insight or attitude that we need to cultivate over the next year or so to make for a better America?

I think for a better America, we should all try to get rad and not give a shit.

I think if most people did that, everything would be just fine. I truly, truly believe that. People ask, "What's getting rad?" It's like—just go out there and find out. Just go do some cool shit. Have some fun. Challenge yourself. Do something you've never done. Go somewhere you've never gone.

Don't worry about what people think of you. Just go get rad. And then, when people think worse of you, tell them to fuck off.

Just stop giving a shit about what other people think and say about you. It is the most freeing and wonderful thing in the world because then you won't give a shit about other people, meaning you're not going to judge them.

And when we don't judge each other, we are much more likely to flourish. And then other people can get rad, and we can all high-five each other and celebrate what should be the Gen X golden years.

All right. That's spoken—it's like you were channeling Madame Macron, right?

HELLO! My name is Brigitte. La la la la. I don't believe that old kid. And so on. She's got three kids who look like exactly like her.

One last question before the last—

—before the last question. Yep.

No, you're making me think of Tucker Carlson, a former Fox News heavyweight who clearly believes every conspiracy that comes down the line. Do you worry about that virus taking over your brain?

My personal brand, no. I think conspiracy theories are fun. I very much believe in Bigfoot. And no one will ever talk me down from that ledge.

But there's a lot of stuff where I'm like, "No, that's just made up." That's just laziness. You're not adequately trying to investigate something, and you can't accept it. Sometimes we just don't know the answer and that's sad for us. And maybe at some point we will.

Then I ask ChatGPT if we're going to be best friends forever. And ChatGPT says, "Fuck yeah." And then I feel better about everything.

All right, we're going to leave it there. We've been talking to Kennedy. Thank you so much.

VIdeo editor: Cody Huff

The post Kennedy: A Gen X Rebel's Journey From MTV to Fox News appeared first on Reason.com.

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